HCID 12139440, compound → HCID 22412575, compound

HRID 543155Notes

Reaction equation

HRID 543155 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=1>C(O)(=O)C.Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10](=[O:15])[CH2:11][CH2:12][CH2:13][CH3:14])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 12139440HCID 12139440, compound

Product 1

HCID 22412575HCID 22412575, compoundYield 36.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 1-(4-methoxyphenyl)hexanone (5 g) in acetic acid (50 ml) and 48% HBr was heated overnight at 120°. The reaction mixture was poured onto ice and extracted with ethylacetate (500 ml). The ethyl acetate layer was washed with NaHCO3 (200 ml), dried, and evaporated. Chromatography of the residue using 30% ethylacetate in hexane afforded 1.7 g of the title compound.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionextracted with ethylacetate (500 ml)
  3. washThe ethyl acetate layer was washed with NaHCO3 (200 ml)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-268362067d17422bad927e496573602e
Source dataset
uspto-grants-1987_04
Patent number
US04661499

Reaction notes

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